Inspired by the books “Thinking in Bets” by Annie Duke , and “Skin in the game” by Nassim Nicholas Taleb each month I will place a $50 bet (or a $50 position) on something I think will or won’t happen.
I am doing this for 3 main reasons
1. To learn more about the world
Like all people, I too hate losing money, so this exercise will force me to alert to and watch out for opportunities within the world. As the cash will be coming out of my pocket I will personally feel any loss incurred.
2. Small downside, significant upside
If I lose all my money every month, then at the end of the year I will be down $600. However if I stumble across the next Bitcoin circa 2013 then there is potential for a huge windfall.
3. Aid understanding
Placing these bets will allow me to evaluate my thought process through feedback from reality. Hopefully learning how to make better decisions along the way.
At the end of each year I will do an accounting of how well or poorly I did, and reflect on the mistakes I have made and blind spots I have.
For some background on the books mentioned earlier check out these resources:
Annie Duke on the Art of Manliness Podcast:
Nassim Nicholas Taleb discussing “Skin in the Game” at a talk at Google: